反应详情

To a solution of benzyl alcohol (3.45 mL, 33.3 mmol) in 1,2-dimethoxyethane (80 mL) was added n-butyl lithium (2.6M hexane solution, 13.5 mL, 33.3 mmol) dropwise, which was then stirred for 10 minutes. Copper(I) chloride (5210 mg, 49.45 mmol) was added thereto, followed by stirring for 10 minutes on an ice bath, then, it was stirred for 2.5 hours at room temperature. 2-Iodothiophene (4995 mg, 23.78 mmol) and pyridine 320 mL were further added, and the solution was stirred for 13 hours under reflux. Ethyl acetate was added to the reaction mixture, which was sequentially washed with 1N hydrochloric acid, an aqueous solution of sodium hydrogen sulfate and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (420 mg, 2.21 mmol, 9.5%) was obtained.

1. stirringby stirring for 10 minutes on an ice bath
2. stirringit was stirred for 2.5 hours at room temperature
3. stirringthe solution was stirred for 13 hours
4. temperatureunder reflux
5. washwas sequentially washed with 1N hydrochloric acid
6. dry with materialan aqueous solution of sodium hydrogen sulfate and brine, dried over anhydrous magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate)